N-(3-isopropylphenyl)-4-methyl-3-nitrobenzamide | 870221-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-isopropylphenyl)-4-methyl-3-nitrobenzamide
• 英文别名: N-(3-isopropyl-phenyl)-4-methyl-3-nitro-benzamide；4-methyl-3-nitro-N-(3-propan-2-ylphenyl)benzamide
• CAS: 870221-10-6
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: ZYUNRJDPXZZXIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-isopropylphenyl)-4-methyl-3-nitrobenzamide 在 钯 氢气 、 silica gel 作用下， 以 乙酸乙酯 、 hexanes 为溶剂， 反应 72.0h， 生成 N-(3-isopropylphenyl)-4-methyl-3-aminobenzamide
  参考文献：
  名称：

  Protein kinase modulators and method of use

  摘要：

  本发明涉及具有一般式I的化合物，其中A、B、D、E、G、H1-5和R1-4在此定义，并且合成中间体，它们能够调节各种蛋白激酶受体酶，并因此影响与这些激酶活动相关的各种疾病状态和条件。例如，这些化合物能够调节激酶酶，从而影响血管生成过程并治疗与血管生成相关的疾病和其他增生性疾病，包括癌症和炎症。本发明还包括包括这些化合物的制药组合物和治疗与蛋白激酶活性相关的疾病状态的方法。

  公开号：

  US07880000B2
• 作为产物：
  描述：

  4-甲基-3-硝基苯甲酸 、 3-异丙基苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74.8%的产率得到N-(3-isopropylphenyl)-4-methyl-3-nitrobenzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of bis-aryl ureas and amides based on 2-amino-3-purinylpyridine scaffold as DFG-out B-Raf kinase inhibitors

  摘要：

  By combining the scaffolds of UI-125 and Sorafenib, a series of bis-aryl ureas and amides based on 2-amino-3-purinylpyridine moiety were designed and synthesized as novel DFG-out B-Raf(V600E) inhibitors. Among them, 20c-e, 20g and 21h displayed potent antiproliferative activities against melanoma A375 (B-Raf(V600E)) cell lines with IC50 values of 3.190, 2276, 1.856, 1.632 mu M and 1.839 mu M, respectively, comparable with the positive control Vemurafenib (IC50 = 3.32 mu M). Selected compounds were tested for the ERK inhibition in human melanoma A375 (B-Raf(V600E)) and SK-MEL-2 (B-Raf(WT)) cell lines by Western blot. The results revealed that our compounds inhibited the proliferation of melanoma A375 cells (B-Raf(V600E)) through ERK pathway, without paradoxical activation of ERK in melanoma SK-MEL-2 cells (B-Rat(WT)). Eventually, 20g and 21h were selected to confirm their inhibitory effects on tumor growth in A375 xenograft models in mice. Compound 20g exhibited equivalent antitumor efficacy in vivo (T/C = 44.37%), compared to Sorafenib (T/C = 37.35%), by 23-day repetitive administration of a single dose of 50 mg/kg without significant body weight loss. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.039

文献信息

• Protein kinase modulators and method of use
  申请人：Geuns-Meyer D. Stephanie

  公开号：US20060009453A1

  公开（公告）日：2006-01-12

  The present invention relates to chemical compounds having a general formula I wherein A, B, D, E, G, H 1-5 and R 1-4 are defined herein, and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of these kinases. For example, the compounds are capable of modulating kinase enzymes thereby influencing the process of angiogenesis and treating angiogenesis-related diseases and other poliferative disorders, including cancer and inflammation. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of protein kinases.

  本发明涉及具有通式I的化合物，其中A、B、D、E、G、H1-5和R1-4在此定义，并且合成中间体，这些化合物能够调节各种蛋白激酶受体酶，从而影响与这些激酶活性相关的各种疾病状态和条件。例如，这些化合物能够调节激酶酶，从而影响血管生成的过程，并治疗与血管生成相关的疾病和其他增生性疾病，包括癌症和炎症。本发明还包括包括这些化合物的药物组合物和治疗与蛋白激酶活性相关的疾病状态的方法。
• Multi-cyclic compounds and methods of use
  申请人：Hodous Brian L.

  公开号：US20080255205A1

  公开（公告）日：2008-10-16

  The present invention relates to compounds of Formulas I and II, wherein B 1 , B 2 , B 3 , B 4 , C 1 , C 2 , ring D, L 1 , L 2 and R 1-4 are defined herein, synthetic intermediates, and pharmaceutical compositions, comprising such compounds. The compounds and compositions are capable of modulating various protein kinase receptors such as Tie-2 and Aurora and, therefore, influencing kinase related disease states and conditions. The compounds, for example, are capable of treating cancer caused by unregulated angiogenesis, and inflammation as well as other proliferative disorders.

  本发明涉及公式I和II的化合物，其中B1、B2、B3、B4、C1、C2、环D、L1、L2和R1-4在此被定义，合成中间体和包含此类化合物的制药组合物。这些化合物和组合物能够调节各种蛋白激酶受体，例如Tie-2和Aurora，从而影响激酶相关的疾病状态和情况。例如，这些化合物能够治疗由未受调节的血管生成引起的癌症和炎症以及其他增殖性疾病。
• MULTI-CYCLIC COMPOUNDS AND METHODS OF USE
  申请人：HODOUS Brian L.

  公开号：US20120245206A1

  公开（公告）日：2012-09-27

  The present invention relates to compounds of Formulas I and II, wherein B 1 , B 2 , B 3 , B 4 , C 1 , C 2 , ring D, L 1 , L 2 and R 1-4 are defined herein, synthetic intermediates, and pharmaceutical compositions, comprising such compounds. The compounds and compositions are capable of modulating various protein kinase receptors such as Tie-2 and Aurora and, therefore, influencing kinase related disease states and conditions. The compounds, for example, are capable of treating cancer caused by unregulated angiogenesis, and inflammation as well as other proliferative disorders.

  本发明涉及I和II式化合物，其中B1、B2、B3、B4、C1、C2、环D、L1、L2和R1-4在此定义，以及合成中间体和含有这些化合物的制药组合物。这些化合物和组合物能够调节各种蛋白激酶受体，如Tie-2和Aurora，从而影响激酶相关的疾病状态和条件。例如，这些化合物能够治疗由未受调节的血管生成引起的癌症和炎症以及其他增殖性疾病。
• PROTEIN KINASE MODULATORS AND METHOD OF USE
  申请人：GEUNS-MEYER Stephanie D.

  公开号：US20110201602A1

  公开（公告）日：2011-08-18

  The present invention relates to chemical compounds having a general formula I wherein A, B, D, E, G, H 1-5 and R 1-4 are defined herein, and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of these kinases. For example, the compounds are capable of modulating kinase enzymes thereby influencing the process of angiogenesis and treating angiogenesis-related diseases and other proliferative disorders, including cancer and inflammation. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of protein kinases.

  本发明涉及具有一般式I的化合物，其中A、B、D、E、G、H1-5和R1-4在此定义，并且合成中间体，这些化合物能够调节各种蛋白激酶受体酶，并因此影响与这些激酶活性相关的各种疾病状态和条件。例如，这些化合物能够调节激酶酶，从而影响血管生成过程，治疗与血管生成相关的疾病和其他增殖性疾病，包括癌症和炎症。本发明还包括包括这些化合物的制药组合物和治疗与蛋白激酶活性相关的疾病状态的方法。
• [EN] NITROGENATED HETEROCYCLIC DERIVATIVES AS PROTEIN KINASE MODULATORS AND USE FOR THE TREATMENT OF ANGIOGENESIS AND CANCER<br/>[FR] MODULATEURS DE PROTEINES KINASES ET PROCEDE D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2005113494A3

  公开（公告）日：2006-03-16